Italy Tours in Winter
Planning for a trip to Italy during Winter? We offer 180 tour packages to Italy departing in Winter that have 2,800 customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Italy on your Winter holiday.
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New Year 2026 exclusive deals on Italy Winter tours — limited-time massive savings on premium travel packages!
Curated by Alessandra Galassi
Italy travel expert at Bookmundi
Our 5-Day Tour offers a perfect blend of history, culture, and natural beauty. Start by exploring the vibrant streets of Naples before embarking on a scenic day trip to the stunning towns of Sorrento, Positano, and Amalfi. The next day, hop on a ferry to the beautiful island of Capri, where you can wander through charming streets, enjoy panoramic views from Augustus Gardens, and see the iconic Faraglioni rocks. Finally, step back in time with a guided tour of Pompeii’s ancient ruins, uncovering the fascinating history of this Roman city. With expert guides, unforgettable sights, and plenty of free time to explore, this tour is the perfect Italian getaway.
5 days
Dive headfirst into Europe’s greatest hits with the European Escapade—a 24-day whirlwind tour that starts and ends in London. From Amsterdam’s canals to the romance of Paris, the energy of Berlin, and the sun-soaked streets of Barcelona, this trip packs in legendary cities, Swiss Alps adventures, and exclusive Special Stays at Hopfgarten and Contiki’s Château de Cruix.
Tailored for young adults, this group tour delivers big on iconic sights, lively social scenes, and memorable moments. Upgrade to the ‘Plus’ for twin-share hotel comfort instead of the classic multi-share.
USP: An expertly curated city sightseeing tour package designed for those who want maximum Europe in minimum time—plus the perks of exclusive accommodations and unforgettable group experiences.
24 days
Experience authentic Italian living on the "Local Living Italy—Sorrento" trip, a seven-day trekking and hiking adventure based in the enchanting town of Sorrento. Perfect for travelers who yearn to go beyond surface sightseeing, this guided tour immerses you in the rhythms of daily life along the Amalfi Coast.
Your journey begins and ends in Naples, with highlights including coastal walks, an excursion to the fashionable island of Capri, and a guided visit to the archaeological marvel of Pompeii. The experience is elevated by your stay on an organic lemon farm, where a local family hosts you and introduces you to the secrets of limoncello making and the joys of Italian agriturismo.
With all accommodations, transport, and meals taken care of, you’re free to soak up the region’s stunning landscapes and savor its renowned cuisine. The unique selling point of this tour package lies in its deep cultural immersion—offering you the chance to live, eat, and explore like a true local. If you’re searching for a trip that blends trekking, culinary delights, and authentic hospitality, this Sorrento adventure is the perfect way to live your Italian dream.
7 days
Experience the full spectrum of Italian wonders on the 'Wonders of Italy' tour, an 11-day guided city sightseeing adventure starting and ending in Rome. Journey through Lucca, Florence, and Venice, cruise along Cinque Terre’s coastline, and savor a glass of Tuscan Chianti. Perfect for travelers who seek rich experiences at an easy pace, this tour package covers hotels, meals, and all transport. The unique selling point is the hands-on discovery of local crafts, including Venetian glassblowing, which adds depth to the exploration. For anyone longing for an immersive Italian journey, this trip brings the country’s artistry and flavors to life.
11 days
Craving a taste of Italy’s most iconic UNESCO sites in just five days? The "Italy City Break" is your passport to a whirlwind of art, history, and vibrant culture. Starting from Rome, you’ll journey to the medieval town of Assisi—birthplace of St Francis—before heading to Florence, the city where the Renaissance began.
Wander through Florence’s architectural marvels, then continue north to explore the artistic treasures of Bologna, Padua, and the canals of Venice. The adventure doesn’t stop there; Tuscany’s world-renowned vineyards invite you for a final taste of la dolce vita before a return to Rome.
Tailored for young adults and seasoned travelers who appreciate efficient yet immersive sightseeing, this trip ensures you soak up Italy’s best in record time. The guided tour package includes essential highlights, expert insights, and a seamless travel experience.
USP: A curated route through Italy’s cultural heartlands, blending world heritage sites, culinary delights, and breathtaking scenery—making it a perfect short escape for those who want to experience Italy’s essence without compromise.
5 days
Dreaming of Italy’s classic wonders? The “Rome, Florence & Venice – 8 Days” sightseeing tour is perfectly tailored for experienced travelers and seniors seeking a comfortable yet enriching exploration of central Italy. Over eight days, travel by coach through Rome, Florence, and Venice, uncovering Renaissance architecture, medieval towns, and vibrant city life.
Enjoy guided walks through Rome, skip the line to marvel at St Peter’s Basilica and the Sistine Chapel, and lose yourself in Florence’s artistic treasures. Visit Siena’s medieval streets, savor Montepulciano’s Tuscan charm, and take in Bologna’s lively ambiance. In Venice, wander romantic canals and discover hidden gems with an expert guide.
This trip’s unique selling point is its comprehensive itinerary: it covers all the must-see sights and hidden corners, with expert commentary, included accommodations, and seamless transport—making it the ideal tour package for those who want to experience Italy’s highlights in comfort and style.
8 days
Discover some of Italy’s essentials during this six-day cultural trip. Visit the Eternal City of Rome, the National and the Vatican Museums. Explore Florence’s unique artistic and cultural centre. Discover the small medieval town of San Gimignano and stop by a typical Tuscan winery where you will visit the cellars and vineyards. Marvel at Siena’s gorgeous architecture and beautiful Main Square.
6 days
The Amalfi Coast’s dramatic cliffs and pastel villages are yours to discover on the “Walking the Amalfi Coast” tour, an eight-day trekking adventure starting and ending in Bomerano. Designed for experienced travelers, this moderate-level trip features expertly guided walks through storied towns like Positano, Ravello, and Amalfi itself.
Follow ancient paths across hillsides, explore the haunting remains of Pompeii, and ascend Mount Vesuvius for sweeping views over the Bay of Naples. The highlight is the legendary Path of the Gods, hailed as one of the world’s greatest coastal walks. Enjoy the warm hospitality of a family-run hotel in the quiet village of Bomerano, away from crowded tourist spots.
All accommodations, meals, and transport are included, ensuring a relaxed and immersive experience. The main activity is trekking, supported by decades of local expertise. A special feature of the tour is the combination of iconic walks and authentic Italian hospitality, making it a standout for lovers of both nature and culture.
For a trip that blends Italy’s best scenery, history, and cuisine, this Amalfi Coast adventure is hard to beat.
8 days
Rome, Florence, Venice—names that conjure centuries of art, culture, and history. The Jewels of Italy tour is a 7-day guided adventure that encapsulates the essence of Italy’s most enchanting cities, designed with both seniors and experienced travelers in mind. Explore the Leaning Tower of Pisa, marvel at Florence’s Duomo, and glide through Venice’s Grand Canal. With comfortable accommodation, included meals, and expert guides, this easy-paced trip ensures you enjoy every landmark without the rush. The USP: a thoughtfully curated tour package that delivers Italy’s timeless magic in just one unforgettable week, perfect for families and culture lovers alike.
7 days
Italy’s treasures await on the "Italian Discovery"—an 11-day journey that sweeps you through Rome, Florence, Sorrento, and beyond. Perfect for families, seniors, and young adults alike, this group tour showcases Renaissance splendors, Roman ruins, and the sun-drenched Amalfi Coast. Guided walks (2–3 miles a day) reveal the essence of each destination, from Florence’s art-filled streets to Sorrento’s seaside charm. Practical details—like euro tips and luggage limits—are handled, and the itinerary blends Northern and Southern Italy for a comprehensive experience. The unique selling point is its family-friendly structure, offering flexibility, expert guidance, and the chance to see Italy’s icons in comfort and style.
11 days
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Most popular Italy Winter Tours
Join one of these handpicked Italy Winter tour packages, tailored to the season.
The Amalfi Coast’s dramatic cliffs and pastel villages are yours to discover on the “Walking the Amalfi Coast” tour, an eight-day trekking adventure starting and ending in Bomerano. Designed for experienced travelers, this moderate-level trip features expertly guided walks through storied towns like Positano, Ravello, and Amalfi itself.
Follow ancient paths across hillsides, explore the haunting remains of Pompeii, and ascend Mount Vesuvius for sweeping views over the Bay of Naples. The highlight is the legendary Path of the Gods, hailed as one of the world’s greatest coastal walks. Enjoy the warm hospitality of a family-run hotel in the quiet village of Bomerano, away from crowded tourist spots.
All accommodations, meals, and transport are included, ensuring a relaxed and immersive experience. The main activity is trekking, supported by decades of local expertise. A special feature of the tour is the combination of iconic walks and authentic Italian hospitality, making it a standout for lovers of both nature and culture.
For a trip that blends Italy’s best scenery, history, and cuisine, this Amalfi Coast adventure is hard to beat.
Winter Departures
26 Dec, 24 Oct
Tour Type
Group Tour
8 days
Rome, Venice, and Florence headline the 'Classical Italy' trip—a 5-day sightseeing tour ideally suited for seniors seeking a taste of Italy’s best cities. With all logistics, hotels, and meals included, this group trip allows you to relax and enjoy the highlights stress-free. The real draw is the concise itinerary—offering maximum cultural impact in a short, easy-paced journey designed to delight mature travelers.
Winter Departures
4 Jan, 11 Jan
Tour Type
Group Tour
5 days
From the sun-drenched hills of Tuscany to the glamour of Capri, 'Italy Bellissimo' is an 11-day city sightseeing tour that captures the spirit of Italy. Starting and ending in Rome, this easy-paced trip takes you through Venice, Montecatini, and more, with highlights including olive oil tasting in an authentic Italian Borgo and evenings spent with new friends. Tailored for those who love culture and conviviality, the tour package covers accommodation, meals, and all transport. Its unique selling point is the seamless blend of classic Italian sights and genuine local experiences, making it an irresistible choice for anyone enchanted by Italy’s charm.
Winter Departures
6 Dec
Tour Type
Group Tour
10 days
The rolling hills and timeless charm of Tuscany await on the "Spotlight on Tuscany" tour, a 9-day art and architecture adventure through Italy’s most cherished region. Starting and ending in Montecatini Terme, this moderate-activity trip is crafted for those who revel in culture, history, and authentic flavors.
Enjoy a 7-night stay in the renowned spa town of Montecatini Terme, your base for exploring Pisa, Florence, San Gimignano, and Lucca—Italy’s best-kept secret. Learn the region’s history at WWII’s Gothic Line and the Museum of Liberation. Delight in hands-on experiences, from a Tuscan cooking class to cheese tastings at a local farm. Savor world-class wines and the region’s celebrated cuisine, and enjoy free time to wander Florence’s artistic treasures.
With accommodations, transport, and meals included, the unique selling point is the blend of immersive culinary and cultural activities, ensuring each traveler connects deeply with the heart of Tuscany in a single, thoughtfully curated tour package.
Winter Departures
2 Dec, 30 Dec
Tour Type
Group Tour
9 days
Explore the crossroads of civilizations on "Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast," a 13-day city sightseeing adventure rich in culture and history. Beginning in Palermo and ending in Rome, this moderately active tour immerses you in Sicily’s ancient wonders and southern Italy’s coastal beauty.
Uncover Palermo’s Moorish and Norman heritage, wander through Cefalù’s seaside splendor, and marvel at the Valley of the Temples in Agrigento. In Taormina, visit a local winery for a tasting and agriturismo dinner—an authentic taste of Sicilian life. Journey to the ancient cave dwellings of Matera before exploring Sorrento and Positano, the pearls of the Amalfi Coast. Walk in the footsteps of Romans at Pompeii’s evocative ruins.
With all accommodations, transport, and meals included, this group tour’s unique selling point is its artful blend of ancient monuments, spectacular coastlines, and local culinary experiences—making it the perfect package for those eager to soak up the essence of southern Italy and Sicily.
Winter Departures
1 Dec, 3 Dec
Tour Type
Group Tour
13 days
From the timeless grandeur of Rome to the sun-drenched cliffs of the Amalfi Coast, this 10-day Italy tour is a feast for the senses and the soul. Designed for travelers eager to explore at a moderate pace, this guided journey immerses you in the heart of Roman history and the breathtaking beauty of southern Italy’s coastline.
Begin with Rome’s legendary sights: an in-depth exploration of the Colosseum and the city’s classic treasures. Journey south to the scenic wonders of the Amalfi Coast, where dramatic coastal vistas and the inviting charm of Sorrento await. Dive into the past at Pompeii’s evocative ruins and wander the hallowed halls of Montecassino’s famed monastery.
But the experiences aren’t just visual—savor authentic mozzarella during a hands-on demonstration, sample the region’s prized Lacryma Christi wine at a local vineyard, and refresh with a taste of traditional limoncello. Throughout, enjoy comfortable accommodations, seamless transport, and expertly guided tours.
What truly sets this tour package apart is its harmonious blend of iconic landmarks, culinary delights, and cultural encounters, delivering an immersive taste of Italy’s rich history and coastal allure for those who crave both discovery and indulgence.
Winter Departures
9 Dec, 14 Dec
Tour Type
Group Tour
10 days
Italy’s treasures await on the "Italian Discovery"—an 11-day journey that sweeps you through Rome, Florence, Sorrento, and beyond. Perfect for families, seniors, and young adults alike, this group tour showcases Renaissance splendors, Roman ruins, and the sun-drenched Amalfi Coast. Guided walks (2–3 miles a day) reveal the essence of each destination, from Florence’s art-filled streets to Sorrento’s seaside charm. Practical details—like euro tips and luggage limits—are handled, and the itinerary blends Northern and Southern Italy for a comprehensive experience. The unique selling point is its family-friendly structure, offering flexibility, expert guidance, and the chance to see Italy’s icons in comfort and style.
Winter Departures
25 Jan, 22 Feb
Tour Type
Group Tour
11 days
Set off from Rome on the 'Italy and Switzerland' tour, a 9-day sightseeing journey through Italy’s capital and beyond. With hotels, transportation, and meals all included, this guided group trip lets you discover the best of Italy in a relaxed, senior-friendly manner. The highlight of this tour is its cross-border perspective—offering a taste of Swiss culture alongside Italian classics, all without the challenges of a demanding itinerary. It’s an easy, enriching escape for those eager to broaden their horizons.
Winter Departures
4 Jan, 11 Jan
Tour Type
Group Tour
9 days
Discover some of Italy’s essentials during this six-day cultural trip. Visit the Eternal City of Rome, the National and the Vatican Museums. Explore Florence’s unique artistic and cultural centre. Discover the small medieval town of San Gimignano and stop by a typical Tuscan winery where you will visit the cellars and vineyards. Marvel at Siena’s gorgeous architecture and beautiful Main Square.
Winter Departures
16 Jan, 17 Jan
Tour Type
Group Tour
6 days
For those fascinated by spirituality and art, the 'Shrines of Italy' tour is a pilgrimage through Italy’s most revered religious and architectural landmarks. This 11-day trip, tailored for seniors and experienced travelers, begins and ends in Rome, guiding you through sacred sites in Assisi, the Amalfi Coast & Campania, and beyond.
Reflect at the Basilica of St. Francis, marvel at the Sistine Chapel’s grandeur, and explore ancient Christian catacombs. Attend a Papal audience, and receive a blessing from the Holy Father, making this journey not only a tour but a deeply meaningful experience. Visit the Grotto of Michael the Archangel, the cathedral of Salerno, and the historic abbey of Montecassino.
The standout element of this tour is its rare blend of faith, art, and history—offering an enriching itinerary that connects travelers with Italy’s spiritual heart through exclusive experiences and guided visits to the world’s most inspirational sites.
Winter Departures
27 Jan, 14 Apr
Tour Type
Group Tour
11 days
See all Italy Winter Tours
Top Italy Tour Activities for Winter
From art architecture tours to city sightseeing and others, here are some popular tour activities in Italy with departures in Winter.
Italy Winter Tours for all Age Groups
Italy tours in Winter designed for all ages—families, young adventurers, seniors, and everyone in between.
Reviews of our Italy Tours for Winter
Feedback from guests who toured Italy during Winter.
Dawn A. | Traveled in December
Paolo was amazing especially when one of the girls had her passport taken from her safe in her room-he helped her get what she could get done and then she went to Florence with us -- walking tours were a little long but all was good
Agnes S. | Traveled in December
The Best of Italy was the best! Our travel director took care of everything and we were able to relax, enjoy, and see Italy in all its glory! It was an incredible trip and would highly recommend Trafalgar!
Jessica B. | Traveled in December
I had an amazing experience with my trip manager Hannah and crew! Hannah was lovely and so personable, I felt completely comfortable asking for help when needed. The itinerary of Italian Espresso was amazing, ticking all the boxes and allowing for free time as well!
William C. | Traveled in December
Love staying in one hotel. Really enjoyed seeing the owner of hotel every day in hotel and around town. Paolo was fantastic. Genuinely cared about us. Great daytime tours. Love the added stop to see The American war cemetery You can tell the vendors / hosts enjoy their relationship with Collette.
John L. | Traveled in December
My tour was fantastic. Everything about it. From our tour guide to the local guides, to the accommodations. To choose just one experience as my favorite would be impossible. Every day was a joy. Many times, after a couple of weeks you are looking forward to going home, despite a good experience. On our last day of this tour, and I know many others felt this way too, I found myself wishing we had more days and I wanted more. In the words of a famous American actor, I'll Be Back!
Sebastian B. | Traveled in December
An extremely well thought-out and organized trip that catered to people from different backgrounds and of different interests. The accommodation, itinerary, and order of activities all made sense, and the staff took all of the stress out of travel to maximise the fun.
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